Water → N-(3-acetyl-benzo[b]thiophen-2-yl)-ethanesulfonamide

HRID 1511500Notes

Reaction equation

HRID 1511500 reaction equation
[Sn](Cl)(Cl)(Cl)Cl.[C:6](Cl)(=[O:8])[CH3:7].[S:10]1[C:14]([NH:15][S:16]([CH2:19][CH3:20])(=[O:18])=[O:17])=[CH:13][C:12]2[CH:21]=[CH:22][CH:23]=[CH:24][C:11]1=2.O>ClCCl>[C:6]([C:13]1[C:12]2[CH:21]=[CH:22][CH:23]=[CH:24][C:11]=2[S:10][C:14]=1[NH:15][S:16]([CH2:19][CH3:20])(=[O:18])=[O:17])(=[O:8])[CH3:7]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 24287Tin tetrachlorideHCID 57920420Ethanesulfonic acid benzo[b]thiophen-2-ylamide

Product 1

HCID 57920498N-(3-acetyl-benzo[b]thiophen-2-yl)-ethanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Tin (IV) chloride (173 μL, 1.48 mmol) was added to a solution of acetyl chloride (124 μL, 1.75 mmol) in dichloromethane (10 mL), at 0° C., and the resulting solution was stirred for 5 min. To the resulting mixture was then added a solution of ethanesulfonic acid benzo[b]thiophen-2-ylamide (325 mg, 1.35 mmol) in dichloromethane (2 mL) at 0° C. The resulting solution was allowed to warm to ambient temperature and then stirred overnight. The resulting solution was treated with water (10 mL), the organic layer separated, dried over sodium sulfate, filtered, and the solvent evaporated in vacuo to yield N-(3-acetyl-benzo[b]thiophen-2-yl)-ethanesulfonamide as a colorless solid. 1H-NMR (DMSO-d6): δ 1.25 (t, 3H), 2.71 (s, 3H), 3.39 (q, 2H), 7.34-7.48 (m, 2H), 7.94 (d, 1H), 8.10 (d, 1H); MS: m/z 284.1 (MH+).

Workup

  1. stirringstirred overnight
  2. customthe organic layer separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-e44525fc80ba440bae683abb6d26f537
Source dataset
uspto-grants-2012_07
Patent number
US08216547B2

Reaction notes

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